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How Women Build Confidence Through Connection with Jillian Johnson

How Women Build Confidence Through Connection with Jillian Johnson

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What if confidence isn't something you find... but something you build?

In this week's conversation, Penny sits down with Jillian Johnson, founder of LEGS (Ladies Executive Golf Society), to explore how connection, community, and a little bit of courage can transform the way women show up in their lives and businesses.

While golf may have brought these women together, this conversation is really about something much bigger: creating opportunities, embracing joy, and stepping into spaces where we may not have always felt invited.

Jillian shares how she went from corporate employee benefits consulting to building a national organization designed to help women feel confident, connected, and empowered through golf.

They also explore why play matters, how community supports our mental health, and why women deserve spaces that encourage collaboration over competition.

Please note: This episode includes discussion of trauma and attempted assault. Listener discretion is advised.

In this episode:

• How Jillian turned an idea into a national community for women
• Why confidence is built through connection and experience
• The networking opportunities many women miss and how to change that
• Why fun and play are essential, not optional
• The role community plays in women's well-being
• How to stop worrying about what others think and start showing up authentically

If you've been craving more confidence, meaningful friendships, or permission to try something new, this conversation is for you.

Connect with Jillian:
Website: legs.golf
LinkedIn: Jillian Johnson, founder of #LEGS

When’s the last time you did something just for YOU? 🍷✨
Wine Camp 2026 is your chance to escape, sip fabulous local wines, cruise at sunset, laugh around the fire pit, and soak up the magic of New York’s Finger Lakes.

📍 Dates: July 30–August 2, 2026
🏡 Spots are limited, so grab yours now: https://www.pennyforyourshots.com/winecamp

Bring your besties or come solo—you’ll leave with new favorites either way. Wine Camp 2026 is calling. Are you in?

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